Note: The job is a remote job and is open to candidates in USA. Milestone Inc. is an AI-native Digital Experience Platform focused on enhancing brand visibility across various digital channels. They are seeking a Head of Commercial Strategy & Enterprise Accounts for the hospitality sector, responsible for driving revenue growth, customer success, and strategic account management for key enterprise clients.
Responsibilities
- Own the overall health, growth, retention, & commercial performance of Milestone's enterprise hospitality & travel portfolio
- Serve as a strategic advisor to executive stakeholders, helping customers align digital investments with revenue, distribution, guest acquisition, & business growth objectives
- Lead commercial planning & strategic account development across key enterprise customers
- Directly manage a portfolio of high-value strategic accounts & serve as the executive relationship owner
- Drive measurable customer outcomes tied to direct bookings, revenue growth, AI visibility, guest acquisition, & digital performance
- Lead executive business reviews, strategic planning sessions, renewal discussions, & expansion opportunities
- Navigate complex commercial negotiations involving renewals, cross-sell, upsell, and long-term partnership growth
- Advise customers on commercial strategies spanning Revenue Management, Distribution, Sales, Marketing, Digital Experience, and Direct Booking optimization
- Help customers identify opportunities to improve channel performance, market share, guest acquisition, profitability, and digital competitiveness
- Stay current on industry trends including revenue management, distribution, metasearch, OTAs, AI-driven discovery, and evolving guest behavior
- Translate industry insights into actionable strategies that improve customer business performance
- Position Milestone as a strategic growth partner rather than a technology vendor
- Lead a high-performing Customer Success & Enterprise Account Management organization focused on customer outcomes, adoption, retention, & growth
- Ensure customers maximize value across Milestone's platform ecosystem, including CMS, GEO, AI Search, Local Listings, Schema, Content Studio, Analytics, & AI-powered solutions
- Develop scalable playbooks for onboarding, adoption, executive engagement, expansion, and risk mitigation
- Establish proactive customer health monitoring & success forecasting processes
- Partner with Product & Engineering teams to ensure customer needs influence product strategy & roadmap priorities
- Act as a senior advisor on AI visibility, GEO, SEO, Local, Entity Optimization, Structured Data, and AI-powered customer acquisition
- Design & execute account growth strategies that expand customer engagement and platform adoption
- Identify opportunities to increase customer share of wallet and accelerate business outcomes
- Collaborate with Marketing to develop thought leadership, customer success stories, executive content, and industry initiatives
- Represent Milestone in executive briefings, customer workshops, webinars, conferences, and strategic industry engagements
- Lead, coach, and develop a world-class organization of Enterprise Account Managers and Customer Success leaders
- Foster a culture of ownership, accountability, customer obsession, operational excellence, and commercial thinking
- Create scalable operating frameworks for forecasting, account planning, risk management, executive communication, and growth execution
- Align Sales, Product, Engineering, Marketing, Professional Services, and Support around customer outcomes
- Serve as the executive voice of the customer across the organization
Skills
- 12–18+ years of experience in enterprise account management, customer success, strategic sales, or commercial leadership roles
- Strong experience within hospitality, travel, tourism, or enterprise martech/SaaS environments
- Proven success leading enterprise account management and/or customer success teams including revenue management and channel distribution
- Demonstrated ownership of enterprise portfolio revenue, renewals, retention, and expansion ARR
- Strong executive presence with experience engaging CMOs, CDOs, Revenue Leaders, and senior hospitality executives
- Deep expertise in digital marketing including SEO, GEO, AI search, omnichannel strategy, ABM, and content strategy
- Strong understanding of SaaS platforms, CMS, analytics, structured data, AI search, and digital experience ecosystems
- Experience managing strategic enterprise accounts directly while also leading teams
- Commercial mindset with strong negotiation and forecasting capabilities
- Strong cross-functional leadership and operational execution skills
- Hospitality technology ecosystem experience is a strong plus: PMS, CRS, OTAs, metasearch, loyalty systems, and revenue management platforms
- Bachelor's degree in Business, Marketing, Hospitality, or related field; MBA preferred
- Experience speaking at industry events or contributing to hospitality thought leadership is a plus
Company Overview
Milestone drives online leads and customer acquisition for over 2,000 companies by seamlessly integrating “Experiences” and “Discovery” into its AI-First Digital Experience Platform. It was founded in 1998, and is headquartered in Santa Clara, California, USA, with a workforce of 201-500 employees. Its website is http://www.milestoneinternet.com/.